Synthesis, structure and redox properties of ferrocenylmethylnucleobases

Citations Over Time

Abstract

Ferrocenyl derivatives of thymine 1, cytosine 2, and uracil and of N2-acetylguanine and 2-amino-6-chloropurine have been prepared from reactions of [Fe(η5-C5H5)(η5-C5H4CH2N(CH3)3)] I with the corresponding pyrimidine or purine base. The predominant site of alkylation for thymine and cytosine was N1 while for uracil N3 was preferred. Alkylation of the guanine precursor 2-amino-6-chloropurine yielded two products, the N2-monosubstituted, and the N2,N9-disubstituted, derivatives. Acetyl protection/deprotection of the N2 amino group allowed selective N9-alkylation to yield 2-amino-6-chloro-9-ferrocenylmethylpurine. With N2-acetylguanine alkylation occurred at either the N7 or N9 positions in a ≈3∶1 ratio. The structures of eight compounds were determined by single crystal X-ray analysis. Electrochemical investigations by cyclic voltammetry revealed reversible redox processes for the compounds.

Related Papers

• → A theoretical reinvestigation of the nucleic bases adenine, guanine, cytosine, thymine and uracil using AM1(1987)94 cited
• → Purine and Pyrimidines in Sediments from the Experimental Mohole(1964)11 cited
• → Gas-liquid chromatography of some pyrimidine derivatives(1971)11 cited
• → Allylation of Nucleic Acid-Bases with Triallyl Phosphate(1979)10 cited
• → Incorporation of adenine and uracil into the nucleic acids of Streptococcus bovis(1973)10 cited